Great Expectations Realty - St. Augustine & Jacksonville

Great Expectations Realty - St. Augustine & Jacksonville This Local Family Owned Real Estate Brokerage specializes in Traditional Listings as well as Auction Augustine.
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Searching for your dream home isn’t always a seamless journey on your own, but one thing’s certain: A professional team can make a dream-home miracle happen. As market analysts and negotiation experts, we at Great Expectations are only the most dedicated realty professionals in St. With decades of combined broker experience and passionate problem solving, our growing team meets every new client wi

th the answers they need to feel confident about the next big step. From empty-nesters and first-timers to retirees and high-end sellers, we are there to help you navigate the market without ever compromising the needs that make your journey unique. Each of their partnerships extends beyond a transaction -- it’s our promise to help you invest in a future that exceeds your expectations.

🌴JUST LISTED🌴 $478,900272 Deer Crossing RdSaint Augustine, FL 320864 bedroom, 3 bathroom 📲 The Fearing Team Rachael & Pe...
08/28/2026

🌴JUST LISTED🌴 $478,900

272 Deer Crossing Rd
Saint Augustine, FL 32086
4 bedroom, 3 bathroom

📲 The Fearing Team
Rachael & Pete Fearing
904-352-9318

Welcome to the largest home in the neighborhood which gives you a split floorplan with 4 bedrooms, 3 full bathrooms, and a HUGE 3 car garage. High ceilings and open concept central common areas are ideal for family time and entertaining guests. Granite counters and stainless steel appliances throughout. Enjoy lots of natural light with a water view through the large 3 panel glass sliders really make this home stand out. Large Florida room shares the water view and faces North keeping the sun out of your eyes while enjoying your morning coffee on the porch. Enjoy a community pool, fitness center with workout room, basketball court soccer field and a playground all with a low HOA fee. Sidewalks make this neighborhood walkable, and a perfect location minutes from I-95, historic downtown St Augustine and our beautiful beaches!

08/28/2026

🗝️ St. Augustine, Florida is home to incredible architecture — historic homes and hotels. We recommend taking a tour of these locations:

📍Castillo de San Marcos National Monument
📍Lightner Museum — former Alcazar Hotel
📍Flagler College — former Ponce de Leon Hotel
📍Villa Zorayda Museum — former winter home of Franklin W. Smith, who inspired Henry Flagler to build his hotels!

📍Historic St. Augustine House + Commercial Space 📍$1,975,00050 Charlotte StSaint Augustine, FL 32084An Iconic Corner in ...
08/27/2026

📍Historic St. Augustine House + Commercial Space 📍$1,975,000

50 Charlotte St
Saint Augustine, FL 32084

An Iconic Corner in the Heart of the Historic District positioned at the prominent corner of Charlotte and Hypolita Streets, 50 Charlotte Street presents a truly rare offering in the heart of St. Augustine’s historic district that has been lovingly held as a legacy property by the same family for over 50 years. Just one block from the Matanzas River bayfront, this exceptional property is surrounded by renowned restaurants, boutique shops, and the city’s most celebrated attractions.

📲 Jena Dennis
904-877-4352

With unmatched walkability, high visibility, and constant pedestrian and trolley traffic throughout the day, the location stands among the most desirable in one of Florida’s most iconic destinations. Originally constructed in 1900, this two-story historic building embodies the timeless character and architectural heritage that define St. Augustine. Set on a fully walled lot, the property reveals a private, brick-pavered courtyard shaded by mature trees - an inviting and tranquil retreat that contrasts beautifully with the vibrant energy just beyond its walls. A classic wooden second-story balcony overlooks Charlotte Street, offering a charming vantage point of the lively streetscape with glimpses toward the bayfront.

👉🏽View the full listing here: https://jenadennis.greatexpectationsrealty.us/property/62-261691-50-charlotte-st-FL-32084

🎸🥳🎤 The Sing Out Loud Festival celebrates 10 years of free concerts in September! The 2026 festival will feature 160 e...
08/27/2026

🎸🥳🎤 The Sing Out Loud Festival celebrates 10 years of free concerts in September! The 2026 festival will feature 160 events at 21 venues from Sept 4-27 throughout St. Johns County, Florida!

VENUES
📍Bin 39 Wine Bar
📍Boat Drinks
📍Casa de Vino 57
📍Colonial Oak Music Park
📍DJ’s Clam Shack
📍Dog Rose Brewing
📍Hornski’s Brewing Co.
📍Ink & Barley
📍Jimmy Hula’s
📍Lincolnville Museum and Cultural Center
📍Ponte Vedra Concert Hall
📍Prohibition Kitchen
📍Ragga Surf Café
📍Sarbez
📍Shanghai Nobby’s
📍Spinster Abbott’s
📍St. Augustine Elks Lodge
📍The St. Augustine Amphitheatre
📍The Waterworks
📍Tonevendor Records
📍Tradewinds Lounge

🎸Local artist showcases
Sept. 4-6, Sept. 11-13, Sept. 18-20
Schedule: www.singoutloudfestival.com/september-2026/events-1

🎸Aoife O’Donovan with St. Augustine Bluegrass Unit
Sept. 11 at Spinster Abbott’s

🎸Sam Grisman Project
Sept. 13 at Ponte Vedra Concert Hall

🎸Sing Out Loud Music Business Program
Sept. 23 at Spinster Abbott’s

🎸Sip Out Loud
Sept. 24 at Bin 39
Tickets: sipoutloud.com

🎸St. Augustine Songwriter’s Festival
Sept. 24-27 at multiple venues in St. Augustine

🎸St. Augustine Record Fair
Sept. 27 at The St. Augustine Amphitheatre

FOLLOW: Sing Out Loud Festival

🗝️ Turn-key Riverfront Property $769,0001711 County Road 13 SElkton, FL 32033📲 Jena Dennis 904-877-4352Mid-century charm...
08/26/2026

🗝️ Turn-key Riverfront Property
$769,000

1711 County Road 13 S
Elkton, FL 32033

📲 Jena Dennis
904-877-4352

Mid-century charm meets riverfront serenity at this one-of-a-kind property on the St. Johns River. Set on 1.16 acres with land on both sides of County Road 13, this turnkey property is currently used as an executive retreat, the home is being offered fully furnished with curated designer mid-century pieces and is already listed across multiple short-term rental platforms, making it immediately income-producing. Whether envisioned as a personal vacation getaway or a savvy investment with short-term rental potential when not being used for personal use, this exceptional property delivers both lifestyle and return. Inside, you’ll find a vibrant blend of artful design and thoughtful updates.

The 3-bedroom, 1-bath layout includes two Murphy beds-one in a bedroom/office hybrid space that opens to the living area-and brand-new tile floors, subflooring, baseboards, and windows throughout. Sunlight pours into the living room, framing spectacular river views that stretch out before you like a painting. The kitchen is as stylish as it is functional, with sleek quartz countertops, a colorful backsplash, garden sink, and abundant cabinetry. Outside, the details shine: paver walkways lead through lush gardens to three distinct courtyards, a brand-new pergola, and a beautifully finished patio. Sip morning coffee surrounded by nature, then stroll down to your private boathouse and dock with electricity and a boat lift. A 3-car garage with new doors, a carport for RV parking with plug-in, a new septic system, water softener with aerator, and even a chicken coop-this home offers a lifestyle as flexible as it is serene.

🎃FALL EVENTS in St. Augustine & St. Johns County, Florida: 📸 Photo shows The Pumpkin Festival & Handmade Market at Wesle...
08/26/2026

🎃FALL EVENTS in St. Augustine & St. Johns County, Florida:

📸 Photo shows The Pumpkin Festival & Handmade Market at Wesley Wells Farms on Sept. 26 — a fourth generation farm!

🎸🎙️Sing Out Loud Festival — Sept 4-29

🇪🇸🎉 Aviles Street Festival — Sept 5 from 5-9 PM

🗝️🇪🇸 St. Augustine Founder’s Day — Sept 12 at the Mission Nombre de Dios and Fountain of Youth

🦪🦐 Oyster Roast & Low Country Boil at the GTM Research Reserve — Sept 18

📖📚 St. Augustine Book Festival — Sept 19 at Ximenez-Fatio House Museum

🎸🎤 St Augustine Songwriters Festival— Sept 24-27 in downtown venues

🍹🎭 The Velvet Underground Show: St. Augustine Speakeasy at
The Assembly Room at Art ‘n Motion — Sept 24-Oct 4

🎃🌾Pumpkin Festival & Handmade Market at Wesley Wells Farms — Sept 26

💿 🎶St. Augustine Record Fair at the St. Augustine Amphitheatre — Sept 27

🐶🖼️ Art & Bark in the Park at Lakeside Park in St. Augustine Beach from 11-4 — Sept 27

🎃 Pumpkin Patch at First United Methodist Church — daily through October

🎭🍽️ The Gilded Cage Supper Club: A Murder Mystery Theatre Experience at The Venue in Hastings — Oct 2-3, Oct 24, Oct 30

🪦🕯️Mortality & Mourning: Women in Black — Candlelight Tours at the Ximenez-Fatio House Museum — Oct 2-31

🤠✨ Starlight Stomp: Boots, Bonfires, and Boot Scootin’ at Wesley Wells Farms at 6 pm — October 2

Comment DANCE for the link so you don’t miss out!

🎀🏃‍♂️Pink up the Pace 5K Run/Walk — Oct 3

🐊🍺 Croctober Fest at the St. Augustine Alligator Farm — Oct 3

🌽🚜 Crop Maze at Sykes Family Farms — Oct 3-Nov 1

🇬🇷🥙 St. Augustine Greek Festival at Holy Trinity Greek Orthodox Church of St. Augustine — Oct 10-11

🐴🐎 Cracker Day & Market at the St. Johns County Fairgrounds — Oct 10

🛍️🖼️ Artisans in the Garden at The Woman’s Exchange of St. Augustine - Peña-Peck House — Oct 11 from 12-4:30

🍁🕺 Fall Barn Dance at Quillow Acres in Hastings — Oct 16

🎶🎸 Vilano Music Fest at Hyatt Place — Oct 17

🥃🍖 Bourbon & BBQ at
Tringali Barn to benefit Jimmy Jam at 6 pm — Oct 17

🕯️🎼The Gilded Table — Candlelight Orchestra Dinner Series at The Venue in Hastings — Oct 23

🥇🏃🏾‍♀️Jail Break 5K at The Old Jail — Oct 24

👧🏼🧒🏽Ancient City Kids Day 2026 at Francis Field — Oct 24 from 11-3

🍬🎃 Trick-or-Treating & Harvest Festival at the Ximenez-Fatio House — Oct 24

👻🫣 Estuscary Haunted Trail hosted by the Friends of the GTM Research Reserve — October 29-31

📍UNDER CONTRACT 📍$449,0005296 Timucua CirSaint Augustine, FL 32086📲Jena Dennis 904-877-4352Located on a generous 1.15-ac...
08/25/2026

📍UNDER CONTRACT 📍$449,000

5296 Timucua Cir
Saint Augustine, FL 32086

📲Jena Dennis
904-877-4352

Located on a generous 1.15-acre lot, 5296 Timucua Circle offers privacy, flexibility, and room to grow with no HOA restrictions. Built in 1992 and encompassing 2,142 square feet, this 4-bedroom, 2.5-bath home blends comfortable living with outstanding potential. A large, paved driveway provides abundant parking, including space for recreational vehicles or boats, while mature trees surrounding the rear of the property create a peaceful natural setting. A screened front porch welcomes you inside to wooden floors and high ceilings that give the home an open, airy feel.

Just off the main living area, the garage has been converted into additional finished living space, complete with built-in storage and its own separate exterior entrance. This versatile area connects to a convenient kitchenette and would be ideal for homeschooling, a private office, studio space, or extended guest accommodations. The owner’s suite is thoughtfully positioned for privacy and overlooks the rear screened porch. It features a spacious bath with double vanity and walk-in shower, along with direct access to the kitchenette area, creating flexibility for multi-generational living or a semi-private retreat. On the opposite side of the home, three additional bedrooms share a well-appointed guest bath, maintaining the comfort of a true split floor plan. Outdoor living is a highlight; the property line extends much farther back than the fence on this 1+ acre lot.

🗝️$5 ADMISSION IN AUGUST! Have you visited the Villa Zorayda Museum in St. Augustine, Florida? See the stunning Gilded...
08/25/2026

🗝️$5 ADMISSION IN AUGUST! Have you visited the Villa Zorayda Museum in St. Augustine, Florida? See the stunning Gilded Age architecture that inspired Henry Flagler to build his hotels! 🗝️🏰 The Zorayda was built in 1883 as the winter residence of Franklin W. Smith, utilizing his method of construction, poured concrete and crushed coquina shell. The building is a replica is the Alhambra Palace in Granada Spain.

Through August 31, the museum is offering First Coast neighbors with Throwback Pricing — just $5 admission!

📍83 King Street
St. Augustine, Florida

While you’re there, experience the newest special exhibition, Building America: The Life and Vision of Franklin W. Smith, and discover the incredible story behind the visionary who built one of St. Augustine’s most fascinating landmarks. From the Civil War to the creation of the Villa Zorayda, it’s a story you won’t soon forget.

🏛️ $5 Admission
📍 For residents of St. Johns, Duval, Clay, Flagler, Nassau & Putnam Counties
🗓️ Throughout August
🪪 Valid photo ID required upon arrival.

Whether it’s your first visit or your fifth, there’s never been a better time to rediscover one of St. Augustine’s hidden treasures.

Building America, the Life and Vision of Franklin W. Smith, reflects the ongoing effort to bring Smith’s life and achievements back into public awareness. It traces his early years, his involvement in Boston during the Civil War era, his imprisonment and subsequent presidential pardon (just weeks before Lincoln’s assassination), his lasting impact on architecture in St. Augustine, and his broader vision for America.

Address

105 S Ponce De Leon Boulevard
Saint Augustine, FL
32084

Opening Hours

Monday 9am - 6pm
Tuesday 9am - 6pm
Wednesday 9am - 6pm
Thursday 9am - 6pm
Friday 9am - 6pm
Saturday 9am - 6pm
Sunday 9am - 6pm

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